CN109929536A - A kind of static pressure piezochromic material and preparation method thereof - Google Patents
A kind of static pressure piezochromic material and preparation method thereof Download PDFInfo
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- CN109929536A CN109929536A CN201910217950.2A CN201910217950A CN109929536A CN 109929536 A CN109929536 A CN 109929536A CN 201910217950 A CN201910217950 A CN 201910217950A CN 109929536 A CN109929536 A CN 109929536A
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Abstract
The invention discloses a kind of static pressure piezochromic material and preparation method thereof, the material is with PARA METHOXY PHENYL ACETONITRILE and 4, and 4 '-diphenyl-dimethanals are raw material, is then made by Knoevenagel condensation.Piezochromic material of the invention under different static pressures color change interval can covering visible light (from blue to red fluorescence), and wavelength of fluorescence and static pressure have good quantitative relationship, have huge applications potentiality in pressure capsule system.
Description
Technical field
The invention belongs to field of material technology, specifically, being related to a kind of static pressure causes off-color material and preparation method thereof.
Background technique
Pressure (power) causes fluorescence discoloration to refer to that fluorescence color or/and intensity etc. are adding mechanical force (friction, shearing etc.) or quiet outside
Pressure effect is lower, and there is a phenomenon where reversible changes.The piezallochromy of ground realization, usually during the grinding process by each to different
Property power (stretch, squeeze, shearing) effect.The piezallochromy realized through static pressure, then what is be subject to is isotropism power.Static pressure
Fluorescence discoloration (Piezochromic fluorescence, PCF) material is caused because its fluorescence can continuously change under pressure
Become, possesses very big application potential in fields such as benthoscope, aircraft wind tunnel test and ultra-deep prospect pits.
Currently, to cause photochromic molecule mainly to have several following for the static pressure reported at present: Jilin University professor Lu Ping preparation
Tetraphenyl ethylene carbonitrile derivatives material (application number: 201410186793.0), can respond the external world 7.2GPa static pressure, glow peak
Position can be moved to 530nm from 467nm, and the design of Jilin University Tian Wenjing professor seminar has synthesized high luminous anthrene and spreads out
Biology, the continuous red shift 652nm of fluorescence spectrum 568nm under the Pressure stimulation from 1atm to 7.9GPa.But material is reported at present
Color change is small, can not achieve the adjusting of visible light wave segment limit (blue to red fluorescence).
Summary of the invention
In order to solve the above-mentioned technical problem, the invention discloses a kind of piezochromic materials and preparation method thereof, specific to wrap
Include following steps:
A kind of static pressure piezochromic material specifically carries out as follows:
Take 4,4 ' shown in formula (II)-diphenyl-dimethanal, PARA METHOXY PHENYL ACETONITRILE and organic base shown in formula (III) be dissolved in
In organic solvent, reaction is stirred at room temperature, wait have a large amount of solid particles precipitation when terminate reaction, then by reaction system-
Overnight stand 12h at 20-0 DEG C, to get target product shown in formula (I)；Described 4,4 '-diphenyl-dimethanal with to methoxyl group
The ratio between amount of substance of benzene acetonitrile, organic base is 1:2-2.5:0.24-0.26.
Further, the organic base is preferably sodium methoxide.
Further, the organic solvent is preferably dehydrated alcohol.
Further, the additional amount of the organic solvent is calculated as 5.77-8.33ml/ with the amount of the substance of the organic base
mmol。
Further, the time that is stirred to react is preferably 8-12h.
Further, the post-processing approach of the reaction solution are as follows: the reaction solution is filtered, obtains precipitating and is eluted with methanol
3~5, target product is obtained after natural drying.
Compared with prior art, the beneficial effects of the present invention are:
Piezochromic material of the invention its have the color change interval covering visible light wave band under 1atm-10GPa pressure (blue
Color can be identified visually to red fluorescence 493nm-628nm).Such as: it is blue-fluorescence (493nm) under 1atm, becomes under 4.6GPa
For green (545nm), 7GPa becomes yellow (574nm), finally becomes under 10GPa again red (628nm), and wavelength of fluorescence and
Static pressure has good quantitative relationship, has huge applications potentiality in pressure capsule system.
Certainly, it implements any of the products of the present invention it is not absolutely required to while reaching all the above technical effect.
Detailed description of the invention
The drawings described herein are used to provide a further understanding of the present invention, constitutes a part of the invention, this hair
Bright illustrative embodiments and their description are used to explain the present invention, and are not constituted improper limitations of the present invention.In the accompanying drawings:
Fig. 1 is the solid powder fluorescence spectrum of the present invention at various pressures.
Fig. 2 is the solid state powder fluorescence spectrum peak value and pressure dependence figure of the present invention at various pressures.
Specific embodiment
Carry out the embodiment that the present invention will be described in detail below in conjunction with embodiment, whereby to the present invention how application technology hand
Section solves technical problem and reaches the realization process of technical effect to fully understand and implement.
Embodiment 1
Weigh 4,4 '-diphenyl-dimethanals (II) 4.20g (20mmol), PARA METHOXY PHENYL ACETONITRILE (III) 5.88g (40mmol)
It is dissolved in 30ml dehydrated alcohol with sodium methoxide 0.27g (5mmol).Reaction 10h is stirred at room temperature, when having the precipitation of a large amount of solid particles
Terminate reaction.Then reaction system is put into -20 DEG C of refrigerator overnights and stands 12h, filtered later, precipitating elutes (20mL with methanol
× 3) secondary, white powder, i.e. target product (I) total 8.4g, yield 90.0% are obtained after natural drying.As piezallochromy material
Material.1H NMR(500MHz,CDCl3): δ (ppm) 8.00 (d, J=8.5Hz, 4H), 7.76 (d, J=8.5Hz, 4H), 7.65 (d, J
=8.5,4H), 7.49 (s, 2H), 7.00 (d, J=9Hz, 4H), 3.89 (s, 6H)；MS m/z:468.4(M+).
Embodiment 2
Weigh 4,4 '-diphenyl-dimethanals (II) 4.20g (20mmol), PARA METHOXY PHENYL ACETONITRILE (III) 6.03g (41mmol)
It is dissolved in 30ml dehydrated alcohol with sodium methoxide 0.27g (5mmol).Reaction 10h is stirred at room temperature, when having the precipitation of a large amount of solid particles
Terminate reaction.Then reaction system is put into -20 DEG C of refrigerator overnights and stands 12h, filtered later, precipitating elutes (20mL with methanol
× 3) secondary, white powder, i.e. target product (I) total 8.52g, yield 91% are obtained after natural drying.As piezallochromy material
Material.
Embodiment 3
Weigh 4,4 '-diphenyl-dimethanals (II) 4.20g (20mmol), PARA METHOXY PHENYL ACETONITRILE (III) 5.88g (40mmol)
It is dissolved in 40ml dehydrated alcohol with sodium methoxide 0.26g (4.8mmol).Reaction 10h is stirred at room temperature, wait there are a large amount of solid particles to be precipitated
When terminate reaction.Then reaction system is put into -20 DEG C of refrigerator overnights and stands 12h, filtered later, precipitating is eluted with methanol
(20mL × 3) are secondary, and white powder, i.e. target product (I) total 8.18g, yield 87.4% are obtained after natural drying.As pressure causes
Off-color material.
Embodiment 4
Weigh 4,4 '-diphenyl-dimethanals (II) 4.20g (20mmol), PARA METHOXY PHENYL ACETONITRILE (III) 5.88g (40mmol)
It is dissolved in 40ml dehydrated alcohol with sodium methoxide 0.28g (5.2mmol).Reaction 9h is stirred at room temperature, wait there are a large amount of solid particles to be precipitated
When terminate reaction.Then reaction system is put into -20 DEG C of refrigerator overnights and stands 12h, filtered later, precipitating is eluted with methanol
(20mL × 3) are secondary, and white powder, i.e. target product (I) total 7.89g, yield 84.3% are obtained after natural drying.As pressure causes
Off-color material.
Embodiment 5
Weigh 4,4 '-diphenyl-dimethanals (II) 4.20g (20mmol), PARA METHOXY PHENYL ACETONITRILE (III) 5.88g (40mmol)
It is dissolved in 35ml dehydrated alcohol with sodium methoxide 0.275g (5.1mmol).Reaction 12h is stirred at room temperature, wait there are a large amount of solid particles to analyse
Reaction is terminated when out.Then reaction system is put into -20 DEG C of refrigerator overnights and stands 12h, filtered later, precipitating is eluted with methanol
(20mL × 3) are secondary, and white powder, i.e. target product (I) total 8.54g, yield 91.2% are obtained after natural drying.As pressure causes
Off-color material.
Embodiment 6
Weigh 4,4 '-diphenyl-dimethanals (II) 4.20g (20mmol), PARA METHOXY PHENYL ACETONITRILE (III) 6.03g (41mmol)
It is dissolved in 40ml chloroform with sodium methoxide 0.27g (5mmol).Reaction 12h is stirred at room temperature, termination when having the precipitation of a large amount of solid particles
Reaction.Then reaction system is put into -20 DEG C of refrigerator overnights and stands 12h, filtered later, precipitating elutes (20mL × 3) with methanol
It is secondary, white powder, i.e. target product 2 (I) total 8.71g, yield 93.1% are obtained after natural drying.As piezallochromy material
Material.
Embodiment 7
Weigh 4,4 '-diphenyl-dimethanals (II) 4.20g (20mmol), PARA METHOXY PHENYL ACETONITRILE (III) 5.88g (40mmol)
It is dissolved in 35ml dehydrated alcohol with sodium methoxide 0.27g (5mmol).Reaction 8h is stirred at room temperature, when having the precipitation of a large amount of solid particles
Terminate reaction.Then reaction system is put into -20 DEG C of refrigerator overnights and stands 12h, filtered later, precipitating elutes (20mL with methanol
× 3) secondary, white powder, i.e. target product (I) total 7.74g, yield 82.7% are obtained after natural drying.As piezallochromy
Material.
Embodiment 8
Weigh 4,4 '-diphenyl-dimethanals (II) 4.20g (20mmol), PARA METHOXY PHENYL ACETONITRILE (III) 6.03g (41mmol)
It is dissolved in 30ml chloroform with sodium methoxide 0.281g (5.2mmol).Reaction 11h is stirred at room temperature, when having the precipitation of a large amount of solid particles
Terminate reaction.Then reaction system is put into -20 DEG C of refrigerator overnights and stands 12h, filtered later, precipitating elutes (20ml with methanol
× 3) secondary, white powder, i.e. target product (I) total 8.84g, yield 94.4% are obtained after natural drying.As piezallochromy
Material.
Embodiment 9
Weigh 4,4 ' -4,4 '-diphenyl-dimethanals of diphenyl-dimethanal (raw material (II)) 4.20g (20mmol), to methoxybenzene
Acetonitrile (III) 6.03g (41mmol) and sodium ethoxide 0.281g (5.2mmol) are dissolved in 30ml dehydrated alcohol.Reaction is stirred at room temperature
11h terminates reaction when having the precipitation of a large amount of solid particles.Then reaction system is put into -20 DEG C of refrigerator overnights and stands 12h, it
After filter, precipitating with methanol elute (20ml × 3) it is secondary, white powder, i.e. target product 2Z, 2'Z are obtained after natural drying) -3,
Bis- (2- (4- methoxyphenyl) acrylonitrile) (I) the total 8.01g of 3'- (biphenyl -4,4'- diyl), yield 85.5%.As pressure causes
Off-color material.
Embodiment 10
20mg target product (I) is dissolved in sample by the piezochromic material culture crystal that we will be obtained using volatility process
In good solvent methylene chloride in bottle, not good solvent is then added dropwise thereto, methylene chloride/n-hexane volume ratio is 4:1.
After concussion uniformly, incomplete sealed sample bottle stands and volatilizees to good solvent, can be obtained high quality crystal in one week.Respectively
High-pressure fluorescence test analysis is done at 1atm-10GPa, obtains the fluorescence spectrum under different pressures.It can be seen that its wavelength of fluorescence with
The increase of pressure, continuous red shift, intensity constantly reduce.Its powder fluorescent becomes green, eventually becomes red (such as Fig. 1 from blue
It is shown).Its solid state fluorescence spectrum peak and pressure dependence at various pressures is analyzed simultaneously, and spectrum peak changes from 493nm
To 628nm, good linear relationship (as shown in Figure 2) is presented in pressure and fluorescence spectrum peak value.
Above description has shown and described several preferred embodiments of invention, but as previously described, it should be understood that invention is not
It is confined to form disclosed herein, should not be regarded as an exclusion of other examples, and can be used for various other combinations, modification
And environment, and can be carried out within that scope of the inventive concept describe herein by the above teachings or related fields of technology or knowledge
Change.And changes and modifications made by those skilled in the art do not depart from the spirit and scope of invention, then it all should be in the appended power of invention
In the protection scope that benefit requires.
Claims (6)
1. a kind of static pressure piezochromic material, it is characterised in that: the piezochromic material carries out as follows:
Take 4,4 ' shown in formula (II)-diphenyl-dimethanal, PARA METHOXY PHENYL ACETONITRILE and organic base shown in formula (III) be dissolved in it is organic
In solvent, reaction is stirred at room temperature, reaction is terminated when having the precipitation of a large amount of solid particles, then by reaction system in -20-0
Overnight stand 12h at DEG C, obtained reaction solution are post-treated to get target product shown in formula (I)；Described 4,4 '-biphenyl
The ratio between dicarbaldehyde and the amount of substance of PARA METHOXY PHENYL ACETONITRILE, organic base are 1:2-2.5:0.24-0.26；
2. piezochromic material as described in claim 1, it is characterised in that: the organic base is sodium methoxide.
3. piezochromic material as described in claim 1, it is characterised in that: the organic solvent is dehydrated alcohol.
4. piezochromic material as described in claim 1, it is characterised in that: the additional amount of the organic solvent has with described
The amount of the substance of machine alkali is calculated as 5.77-8.33ml/mmol.
5. piezochromic material as described in claim 1, it is characterised in that: the time that is stirred to react is 8-12h.
6. piezochromic material as described in claim 1, it is characterised in that: the post-processing approach of the reaction solution are as follows: by institute
The reaction solution filtering stated obtains precipitating with methanol elution 3~5, obtains target product after natural drying.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110614813A (en) * | 2019-10-16 | 2019-12-27 | 清远市腾翔皮革有限公司 | Novel leather |
| CN111499573A (en) * | 2020-05-09 | 2020-08-07 | 浙江工业大学 | Pressure-induced color-changing fluorescent molecule and preparation method thereof |
| CN115073780A (en) * | 2022-06-25 | 2022-09-20 | 天津农学院 | Force induced fluorescence enhancement polymer and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104312576A (en) * | 2014-09-01 | 2015-01-28 | 吉林大学 | Piezochromic material, preparation method and applications thereof |
-
2019
- 2019-03-21 CN CN201910217950.2A patent/CN109929536A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104312576A (en) * | 2014-09-01 | 2015-01-28 | 吉林大学 | Piezochromic material, preparation method and applications thereof |
Non-Patent Citations (3)
| Title |
|---|
| GANUSHCHAK, N. I.等: "Catalytic reaction of p,p"-bis(2-cyano-1-ethenyl)biphenyl with aromatic diazonium salts", 《UKRAINSKII KHIMICHESKII ZHURNAL (RUSSIAN EDITION)》 * |
| 冯存方: "氰基取代对苯撑乙烯衍生物的设计合成及光电性质研究", 《中国优秀博硕士学位论文全文数据库(硕士) 工程科技Ⅰ辑》 * |
| 毛文纲等: "基于苯乙烯腈结构的可逆力致变色化合物的合成及性能", 《化学学报》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110614813A (en) * | 2019-10-16 | 2019-12-27 | 清远市腾翔皮革有限公司 | Novel leather |
| CN111499573A (en) * | 2020-05-09 | 2020-08-07 | 浙江工业大学 | Pressure-induced color-changing fluorescent molecule and preparation method thereof |
| CN115073780A (en) * | 2022-06-25 | 2022-09-20 | 天津农学院 | Force induced fluorescence enhancement polymer and preparation method thereof |
| CN115073780B (en) * | 2022-06-25 | 2024-06-04 | 天津农学院 | Force-induced fluorescence enhanced polymer and preparation method thereof |
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